5-BROMOTHIOPHENE-2-CARBONITRILE Chemical Properties

Boiling point:

124°C/34mmHg(lit.)

Density 

1.694 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.6190(lit.)

Flash point:

214 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light orange to Yellow

Specific Gravity

1.619

λmax

276nm(Benzene)(lit.)

InChI

InChI=1S/C5H2BrNS/c6-5-2-1-4(3-7)8-5/h1-2H

InChIKey

YVVHCBNJWHPMCQ-UHFFFAOYSA-N

SMILES

C1(C#N)SC(Br)=CC=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37

RIDADR 

3267

WGK Germany 

3

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

5-BROMOTHIOPHENE-2-CARBONITRILE Usage And Synthesis

Chemical Properties

Colorless liquid or semisolid

Synthesis

General procedure for the synthesis of 5-bromothiophene-2-carboxaldehyde oxime from 5-bromothiophene-2-carbonitrile: To a mixture of 5-bromothiophene-2-carboxaldehyde oxime (1.3 g, 6.2 mmol) and tetrahydrofuran (15 mL), acetic acid (1.4 mL, 25 mmol) and acetic anhydride (1.5 mL, 15 mmol) were added, and the reaction was started at room temperature. Subsequently, the reaction mixture was stirred at 50 °C for 2 hours, then warmed to 70 °C to continue stirring for 8 hours. Upon completion of the reaction, the reaction mixture was cooled and the solvent was removed by vacuum concentration. The crude product was purified by NH-silica gel column chromatography (eluent ratio heptane:ethyl acetate=8:1) to afford 5-bromothiophene-2-carbonitrile (1.0 g, 5.4 mmol, 88% yield) as a colorless solid.1H-NMR (CDCl3) δ (ppm): 7.11 (1H, d, J=4.0 Hz), 7.40 (1H, d, J=4.0 Hz).

References

[1] Patent: EP1782811, 2007, A1. Location in patent: Page/Page column 51
[2] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
[3] Patent: WO2003/87103, 2003, A1. Location in patent: Page/Page column 17
[4] Patent: WO2005/82899, 2005, A1. Location in patent: Page/Page column 30
[5] Synlett, 2011, # 15, p. 2223 - 2227

5-BROMOTHIOPHENE-2-CARBONITRILE(2160-62-5)Related Product Information

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